catena-Poly[[(2-methyl­imidazole)copper(II)]-μ-pyridine-2,6-dicarboxyl­ato]

The reaction of pyridine-2,6-dicarboxylic acid (H₂DPC) and 2-methyl­imidazole (mim) with CuCl₂·6H₂O yields the one-dimensional title polymer, [Cu(C₇H₃O₄)(C₄H₆N₂)]_n. Hydrogen bonds connect the one-dimensional polymer chains into a three-dimensional supra­molecular architecture.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.056
• wR factor = 0.136
• Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       1.95
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      1.949
            Tmax scaled      0.711 Tmin scaled      0.493
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.80
           From the CIF: _reflns_number_total               2516
           Count of symmetry unique reflns         1493
           Completeness (_total/calc)            168.52%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1023
           Fraction of Friedel pairs measured     0.685
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SMART; data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

catena-Poly[[(2-methylimidazole)copper(II)]-µ-pyridine-2,6-dicarboxylato]

Crystal data

[Cu(C7H3O4)(C4H6N2)]	F(000) = 628.0
Mr = 310.75	Dx = 1.775 Mg m^−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 52 reflections
a = 15.490 (3) Å	θ = 2.2–26.0°
b = 11.021 (2) Å	µ = 1.89 mm^−1
c = 6.8124 (14) Å	T = 295 K
V = 1162.9 (4) Å^3	Block, dark green
Z = 4	0.35 × 0.21 × 0.18 mm

Data collection

Bruker APEX area-detector diffractometer	2516 independent reflections
Radiation source: fine-focus sealed tube	2308 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
Detector resolution: 0 pixels mm^-1	θmax = 27.8°, θmin = 1.9°
φ and ω scans	h = −20→14
Absorption correction: multi-scan (SADABS; Bruker, 2002)	k = −14→14
Tmin = 0.253, Tmax = 0.365	l = −8→7
6787 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.056	H-atom parameters constrained
wR(F^2) = 0.136	w = 1/[σ^2(Fo^2) + (0.0669P)^2 + 0.8885P] where P = (Fo^2 + 2Fc^2)/3
S = 1.15	(Δ/σ)max = 0.017
2516 reflections	Δρmax = 0.93 e Å^−3
173 parameters	Δρmin = −0.77 e Å^−3
1 restraint	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.03 (3)

Special details

Experimental. IR (KBr, cm^-1): 3071 (w), 1689 (w), 1605 (vs), 1450 (s), 1418 (s), 1343 (s), 1245 (w), 1020 (m), 750 (m).

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.46482 (3)	0.19941 (4)	0.33192 (17)	0.02669 (19)
C3	0.2879 (3)	0.1509 (4)	0.3427 (10)	0.0243 (10)
N1	0.5610 (3)	0.3069 (4)	0.2760 (7)	0.0274 (12)
O1	0.3746 (3)	0.3220 (3)	0.4074 (7)	0.0341 (10)
N2	0.3648 (2)	0.1008 (3)	0.3111 (8)	0.0212 (8)
C4	0.4670 (3)	−0.0443 (5)	0.2021 (9)	0.0276 (12)
O3	0.5180 (2)	0.0453 (3)	0.2143 (7)	0.0349 (10)
C5	0.2973 (4)	0.2827 (5)	0.4035 (9)	0.0280 (12)
O2	0.2314 (3)	0.3412 (4)	0.4427 (7)	0.0421 (11)
C6	0.3733 (3)	−0.0141 (5)	0.2506 (8)	0.0252 (10)
C7	0.3009 (4)	−0.0870 (5)	0.2306 (9)	0.0331 (13)
H7	0.3062	−0.1683	0.1958	0.040*
C8	0.2205 (4)	−0.0359 (6)	0.2638 (9)	0.0372 (14)
H8	0.1710	−0.0832	0.2508	0.045*
C9	0.2132 (3)	0.0855 (5)	0.3165 (11)	0.0296 (11)
H9	0.1594	0.1215	0.3334	0.036*
O4	0.4848 (3)	−0.1469 (4)	0.1448 (7)	0.0364 (10)
N3	0.6500 (3)	0.4572 (4)	0.2662 (9)	0.0410 (14)
H3A	0.6777	0.5215	0.3000	0.049*
C12	0.5892 (3)	0.4008 (5)	0.3764 (9)	0.0334 (15)
C13	0.6042 (4)	0.3046 (5)	0.1001 (11)	0.0427 (16)
H13	0.5961	0.2481	0.0003	0.051*
C10	0.6601 (5)	0.3975 (6)	0.0963 (13)	0.054 (2)
H10	0.6984	0.4167	−0.0043	0.064*
C14	0.5608 (6)	0.4388 (7)	0.5696 (13)	0.0558 (19)
H14A	0.5266	0.5112	0.5581	0.084*
H14B	0.6101	0.4548	0.6507	0.084*
H14C	0.5266	0.3757	0.6279	0.084*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0206 (3)	0.0183 (3)	0.0412 (4)	−0.0016 (2)	0.0001 (4)	−0.0042 (4)
C3	0.026 (2)	0.027 (2)	0.019 (2)	0.0050 (17)	−0.001 (3)	0.002 (3)
N1	0.024 (2)	0.0206 (19)	0.038 (3)	−0.0008 (16)	−0.0002 (17)	0.0006 (18)
O1	0.028 (2)	0.0182 (16)	0.056 (3)	0.0054 (15)	−0.0015 (18)	−0.0065 (17)
N2	0.0218 (17)	0.0197 (16)	0.022 (2)	0.0009 (14)	−0.007 (2)	0.001 (2)
C4	0.024 (3)	0.024 (3)	0.035 (3)	0.002 (2)	0.006 (2)	0.001 (2)
O3	0.0217 (19)	0.0261 (19)	0.057 (3)	0.0025 (16)	0.0111 (18)	−0.0074 (19)
C5	0.031 (3)	0.022 (2)	0.031 (3)	0.006 (2)	0.000 (2)	0.005 (2)
O2	0.035 (2)	0.042 (2)	0.049 (3)	0.0197 (19)	0.007 (2)	0.000 (2)
C6	0.026 (3)	0.024 (2)	0.025 (2)	0.000 (2)	0.000 (2)	0.001 (2)
C7	0.039 (3)	0.024 (3)	0.035 (3)	−0.004 (2)	0.000 (3)	0.003 (2)
C8	0.034 (3)	0.037 (3)	0.040 (3)	−0.011 (2)	0.000 (2)	0.003 (3)
C9	0.026 (2)	0.035 (2)	0.027 (3)	0.0012 (19)	0.000 (3)	0.007 (3)
O4	0.036 (2)	0.0217 (18)	0.052 (3)	0.0038 (16)	0.013 (2)	−0.0071 (19)
N3	0.031 (3)	0.028 (2)	0.064 (4)	−0.010 (2)	−0.003 (2)	0.009 (2)
C12	0.033 (3)	0.023 (2)	0.045 (4)	−0.001 (2)	−0.007 (2)	−0.001 (2)
C13	0.044 (4)	0.037 (3)	0.047 (4)	0.000 (3)	0.012 (3)	−0.001 (3)
C10	0.050 (4)	0.044 (4)	0.067 (5)	−0.003 (3)	0.031 (4)	0.006 (4)
C14	0.063 (5)	0.041 (4)	0.063 (5)	−0.012 (4)	−0.004 (4)	−0.015 (4)

Geometric parameters (Å, º)

Cu1—N2	1.898 (4)	C7—C8	1.386 (9)
Cu1—N1	1.941 (5)	C7—H7	0.9300
Cu1—O1	2.011 (4)	C8—C9	1.391 (8)
Cu1—O3	2.050 (4)	C8—H8	0.9300
Cu1—O4^i	2.343 (5)	C9—H9	0.9300
C3—N2	1.331 (6)	O4—Cu1^ii	2.343 (5)
C3—C9	1.374 (7)	N3—C10	1.341 (10)
C3—C5	1.517 (7)	N3—C12	1.355 (8)
N1—C12	1.315 (7)	N3—H3A	0.8600
N1—C13	1.373 (8)	C12—C14	1.450 (10)
O1—C5	1.273 (7)	C13—C10	1.341 (9)
N2—C6	1.338 (6)	C13—H13	0.9300
C4—O4	1.228 (7)	C10—H10	0.9300
C4—O3	1.268 (6)	C14—H14A	0.9600
C4—C6	1.525 (7)	C14—H14B	0.9600
C5—O2	1.236 (7)	C14—H14C	0.9600
C6—C7	1.386 (8)
N2—Cu1—N1	164.0 (2)	C7—C6—C4	128.4 (5)
N2—Cu1—O1	80.60 (16)	C6—C7—C8	118.4 (5)
N1—Cu1—O1	100.02 (17)	C6—C7—H7	120.8
N2—Cu1—O3	79.88 (16)	C8—C7—H7	120.8
N1—Cu1—O3	96.90 (17)	C7—C8—C9	120.4 (5)
O1—Cu1—O3	159.33 (17)	C7—C8—H8	119.8
N2—Cu1—O4^i	101.46 (19)	C9—C8—H8	119.8
N1—Cu1—O4^i	94.22 (17)	C3—C9—C8	118.0 (5)
O1—Cu1—O4^i	99.48 (18)	C3—C9—H9	121.0
O3—Cu1—O4^i	90.99 (18)	C8—C9—H9	121.0
N2—C3—C9	121.0 (4)	C4—O4—Cu1^ii	126.3 (4)
N2—C3—C5	110.8 (4)	C10—N3—C12	109.5 (5)
C9—C3—C5	128.2 (4)	C10—N3—H3A	125.2
C12—N1—C13	107.8 (5)	C12—N3—H3A	125.2
C12—N1—Cu1	129.3 (4)	N1—C12—N3	107.7 (5)
C13—N1—Cu1	122.3 (4)	N1—C12—C14	126.8 (6)
C5—O1—Cu1	114.8 (3)	N3—C12—C14	125.5 (6)
C3—N2—C6	122.0 (4)	C10—C13—N1	108.5 (6)
C3—N2—Cu1	118.8 (3)	C10—C13—H13	125.7
C6—N2—Cu1	119.0 (3)	N1—C13—H13	125.7
O4—C4—O3	126.8 (5)	N3—C10—C13	106.4 (6)
O4—C4—C6	118.9 (5)	N3—C10—H10	126.8
O3—C4—C6	114.1 (5)	C13—C10—H10	126.8
C4—O3—Cu1	114.9 (3)	C12—C14—H14A	109.5
O2—C5—O1	126.4 (5)	C12—C14—H14B	109.5
O2—C5—C3	118.6 (5)	H14A—C14—H14B	109.5
O1—C5—C3	115.0 (4)	C12—C14—H14C	109.5
N2—C6—C7	120.0 (5)	H14A—C14—H14C	109.5
N2—C6—C4	111.5 (4)	H14B—C14—H14C	109.5

Symmetry codes: (i) −x+1, −y, z+1/2; (ii) −x+1, −y, z−1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O2^iii	0.86	1.98	2.824 (7)	166

Symmetry code: (iii) x+1/2, −y+1, z.